ES2711122T3 - Preparación de 3-fluoropropil-nor-beta-CIT radioyodado - Google Patents

Preparación de 3-fluoropropil-nor-beta-CIT radioyodado Download PDF

Info

Publication number: ES2711122T3
Authority: ES; Spain
Prior art keywords: compound; reaction mixture; reaction; group; preparation
Prior art date: 2013-09-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES14849233T

Other languages

English (en)

Spanish (es)

Inventor

Edmund C Hudson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Specgx LLC

Original Assignee

Specgx LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2013-09-25

Filing date

2014-09-25

Publication date

2019-04-30

2014-09-25 Application filed by Specgx LLC filed Critical Specgx LLC

2019-04-30 Application granted granted Critical

2019-04-30 Publication of ES2711122T3 publication Critical patent/ES2711122T3/es

Status Active legal-status Critical Current

2034-09-25 Anticipated expiration legal-status Critical

Links

238000002360 preparation method Methods 0.000 title claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 72
238000006243 chemical reaction Methods 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 42
XQNMZKNFKRXLAD-UHFFFAOYSA-N 3-fluoropropanal Chemical group FCCC=O XQNMZKNFKRXLAD-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
239000002168 alkylating agent Substances 0.000 claims abstract description 7
229940100198 alkylating agent Drugs 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
239000011541 reaction mixture Substances 0.000 claims description 44
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
239000003638 chemical reducing agent Substances 0.000 claims description 13
DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 claims description 12
-1 sodium triacetoxyborohydride Chemical compound 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 11
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
238000010520 demethylation reaction Methods 0.000 claims description 7
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
235000009518 sodium iodide Nutrition 0.000 claims description 6
230000017858 demethylation Effects 0.000 claims description 5
239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 3
229910001494 silver tetrafluoroborate Inorganic materials 0.000 claims description 3
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 claims description 3
229960001479 tosylchloramide sodium Drugs 0.000 claims description 3
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 claims description 2
PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 claims description 2
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims 1
238000010791 quenching Methods 0.000 claims 1
230000000171 quenching effect Effects 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 14
239000000203 mixture Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007818 Grignard reagent Substances 0.000 description 11
150000004795 grignard reagents Chemical class 0.000 description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
0 COC(C1=CC[C@@]2*[C@@]1CC2)=O Chemical compound COC(C1=CC[C@@]2*[C@@]1CC2)=O 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000005755 formation reaction Methods 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000002243 precursor Substances 0.000 description 6
MPSNEAHFGOEKBI-VXNVDRBHSA-N Anhydroecgonine methyl ester Chemical compound COC(=O)C1=CC[C@@H]2CC[C@H]1N2C MPSNEAHFGOEKBI-VXNVDRBHSA-N 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
MPSNEAHFGOEKBI-UHFFFAOYSA-N anhydroecogonine methyl ester Natural products COC(=O)C1=CCC2CCC1N2C MPSNEAHFGOEKBI-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
VNHWPVLQRKKKRY-UHFFFAOYSA-N 1-bromo-3-fluoropropane Chemical compound FCCCBr VNHWPVLQRKKKRY-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
NXTVQNIVUKXOIL-UHFFFAOYSA-N N-chlorotoluene-p-sulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCl)C=C1 NXTVQNIVUKXOIL-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical group C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 description 3
UKTSSJJZFVGTCG-UHFFFAOYSA-N (4-bromophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC=C(Br)C=C1 UKTSSJJZFVGTCG-UHFFFAOYSA-N 0.000 description 2
YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 2
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012217 radiopharmaceutical Substances 0.000 description 2
229940121896 radiopharmaceutical Drugs 0.000 description 2
230000002799 radiopharmaceutical effect Effects 0.000 description 2
238000002390 rotary evaporation Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000000935 solvent evaporation Methods 0.000 description 2
229950009390 symclosene Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
HZGRVVUQEIBCMS-HTRCEHHLSA-N (1s,5r)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene-4-carboxylic acid Chemical class C1C=C(C(O)=O)[C@H]2CC[C@@H]1N2C HZGRVVUQEIBCMS-HTRCEHHLSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
NLRJUIXKEMCEOH-UHFFFAOYSA-N 3-fluoropropan-1-ol Chemical compound OCCCF NLRJUIXKEMCEOH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
208000016285 Movement disease Diseases 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
239000008351 acetate buffer Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001335 demethylating effect Effects 0.000 description 1
230000000779 depleting effect Effects 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0446—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K51/0448—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil tropane or nortropane groups, e.g. cocaine

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Optics & Photonics (AREA)
Physics & Mathematics (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ES14849233T 2013-09-25 2014-09-25 Preparación de 3-fluoropropil-nor-beta-CIT radioyodado Active ES2711122T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US201361882039P	2013-09-25	2013-09-25
PCT/US2014/057404 WO2015048250A1 (en)	2013-09-25	2014-09-25	Preparation of radioiodinated 3-fluoropropyl-nor-beta-cit

Publications (1)

Publication Number	Publication Date
ES2711122T3 true ES2711122T3 (es)	2019-04-30

Family

ID=52691501

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES14849233T Active ES2711122T3 (es)	2013-09-25	2014-09-25	Preparación de 3-fluoropropil-nor-beta-CIT radioyodado

Country Status (11)

Country	Link
US (1)	US9339565B2 (pl)
EP (1)	EP3049378B1 (pl)
JP (2)	JP6224256B2 (pl)
AU (1)	AU2014326601B2 (pl)
BR (1)	BR112016006129A2 (pl)
CA (1)	CA2922723C (pl)
ES (1)	ES2711122T3 (pl)
MX (1)	MX382629B (pl)
PL (1)	PL3049378T3 (pl)
TR (1)	TR201901758T4 (pl)
WO (1)	WO2015048250A1 (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011141532A1 (en)	2010-05-12	2011-11-17	Nestec S.A.	Capsule, system and method for preparing a beverage by centrifugation
US9513907B2 (en) *	2013-08-06	2016-12-06	Intel Corporation	Methods, apparatus, instructions and logic to provide vector population count functionality
EP3718569B1 (en)	2015-05-22	2023-05-03	Translational Drug Development, LLC	Benzamide and active compound compositions and methods of use

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4190601A (en) *	1978-05-31	1980-02-26	Union Carbide Corporation	Production of tertiary amines by reductive alkylation
US6123917A (en)	1990-08-09	2000-09-26	Research Triangle Institute	Method for making cocaine receptor binding ligands and intermediates therefor
US5698179A (en) *	1992-02-25	1997-12-16	Neuro Imaging Technologies, Llc	Iodinated neuroprobe for mapping monoamine reuptake sites
JP2001503412A (ja) *	1996-10-29	2001-03-13	ギルフォードファーマシューティカルズインコーポレイテッド	放射性薬剤の製造方法
FI104048B (fi) *	1997-06-16	1999-11-15	Map Medical Technologies Oy	Prosessi tuottaa radiojodattuja reseptoriaineita in vivo käyttöön
CA2285516C (en) *	1999-05-12	2010-12-07	President And Fellows Of Harvard College	Dopamine transporter imaging agents
JP2001213881A (ja) *	2000-02-02	2001-08-07	Nihon Medi Physics Co Ltd	アンヒドロエクゴニン誘導体の合成法
KR100777885B1 (ko) *	2003-10-03	2007-11-28	화이자 인코포레이티드	Ｈｉｖ 및 염증 치료를 위한 ｃｃｒ5 수용체 길항제 활성을갖는 이미다조피리딘 치환된 트로판 유도체
KR100789847B1 (ko) *	2004-12-15	2007-12-28	(주)퓨쳐켐	알코올 용매하에서 유기플루오로 화합물의 제조방법
MX2010005122A (es) *	2007-11-07	2010-08-18	Ge Healthcare Bv	Estabilizacion de radiofarmaceuticos.
CA2752744A1 (en)	2009-02-17	2010-08-26	Mallinckrodt Inc.	Process for the reductive alkylation of normorphinans
GB0922023D0 (en) *	2009-12-17	2010-02-03	Ge Healthcare Ltd	Preparation of n-monofluoroalkyl compounds

2014
- 2014-09-25 CA CA2922723A patent/CA2922723C/en active Active
- 2014-09-25 JP JP2016545225A patent/JP6224256B2/ja active Active
- 2014-09-25 WO PCT/US2014/057404 patent/WO2015048250A1/en not_active Ceased
- 2014-09-25 AU AU2014326601A patent/AU2014326601B2/en active Active
- 2014-09-25 EP EP14849233.3A patent/EP3049378B1/en active Active
- 2014-09-25 US US14/496,376 patent/US9339565B2/en active Active
- 2014-09-25 ES ES14849233T patent/ES2711122T3/es active Active
- 2014-09-25 TR TR2019/01758T patent/TR201901758T4/tr unknown
- 2014-09-25 PL PL14849233T patent/PL3049378T3/pl unknown
- 2014-09-25 BR BR112016006129A patent/BR112016006129A2/pt not_active Application Discontinuation
- 2014-09-25 MX MX2016003035A patent/MX382629B/es unknown
2017
- 2017-09-22 JP JP2017182197A patent/JP6423936B2/ja active Active

Also Published As

Publication number	Publication date
PL3049378T3 (pl)	2019-06-28
WO2015048250A1 (en)	2015-04-02
EP3049378A1 (en)	2016-08-03
EP3049378B1 (en)	2018-12-05
JP2016533390A (ja)	2016-10-27
TR201901758T4 (tr)	2019-03-21
US20150087838A1 (en)	2015-03-26
JP6224256B2 (ja)	2017-11-01
MX382629B (es)	2025-03-13
BR112016006129A2 (pt)	2017-08-01
JP6423936B2 (ja)	2018-11-14
US9339565B2 (en)	2016-05-17
MX2016003035A (es)	2016-06-10
AU2014326601A1 (en)	2016-03-17
CA2922723A1 (en)	2015-04-02
EP3049378A4 (en)	2017-04-19
JP2017218460A (ja)	2017-12-14
CA2922723C (en)	2022-04-19
AU2014326601B2 (en)	2018-01-18

Publication	Publication Date	Title
ES2329739T3 (es)	2009-11-30	Analogos de cocaina.
JP3228422B2 (ja)	2001-11-12	モノアミン再取込み部位のマッピング用ヨウ素付加神経プローブ
JP4500454B2 (ja)	2010-07-14	１，４−ジアザビシクロ［３．２．２］ノナン−４−カルボキシレートおよびカルボキサミド誘導体、治療におけるその製造ならびに使用
JP6093310B2 (ja)	2017-03-08	ボアカンギンからノルイボガインを調製するための方法および組成物
US6908927B2 (en)	2005-06-21	Pyridopyranoazepine derivatives, their preparation and their therapeutic application
ES2384652T3 (es)	2012-07-10	Sales de escopina y su utilización en procedimientos para la preparación de N-demetil-tiotropio y bromuro de tiotropio
JPH03176486A (ja)	1991-07-31	新規三環式化合物
ES2711122T3 (es)	2019-04-30	Preparación de 3-fluoropropil-nor-beta-CIT radioyodado
CN113905735B (zh)	2024-03-15	神经激肽-1拮抗剂
JP2017506226A (ja)	2017-03-02	（２ｓ，５ｒ）−１，６−ジアザ−ビシクロ［３．２．１］オクタン−２−カルボニトリル−７−オキソ−６−（スルホオキシ）−モノナトリウム塩を調製する方法
ES2338054T3 (es)	2010-05-03	Metodos para producir morfinonas 3-o-protegidas y carboxilatos de morfinona dienol 3-o-protegidos.
ES2232947T3 (es)	2005-06-01	Procedimiento para la produccion de agentes neurorrecepetores marcados con yodo radioactio.
CN105503907B (zh)	2018-01-09	对映选择性合成Vinca类生物碱的方法
EP0457243A1 (en)	1991-11-21	Novel tricyclic compounds
US4874601A (en)	1989-10-17	Radiolabelling kit
EP1988086B1 (en)	2011-11-23	Process for resolving citalopram via its (S)-enriched citalopram tartrate compound.
BRPI0719578A2 (pt)	2013-12-17	Composto, composição farmacêutica, uso do composto, e, método para tratamento, prevenção ou alívio de uma doença ou um distúrbio ou uma condição de um corpo de animal vivo
HU188065B (en)	1986-03-28	New process for the dealkylation of tertiary amines
Cevasco et al.	1991	The E1cB mechanism in the alkaline hydrolysis of N, N-diethyl-P-(3, 5-dimethyl-4-hydroxyphenyl) phosphonamidic chloride
JPS5953485A (ja)	1984-03-28	リゼルギン酸誘導体化合物
Meeuwissen et al.	1982	Synthesis and structure of 6‐exo‐hydroxy‐1, 2‐diphenyl‐1‐phosphoniatricyclo [3.3. 1.1] decane iodide, a derivative of 1‐phosphaadamantane